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25D-NM-NDEAOP

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25D-NM-NDEAOP
Clinical data
Other names25D-NM-NDECE; 25D-NM-NDEPA; N-Methyl-N-(3-diethylamino-3-oxopropyl)-2,5-dimethoxy-4-methylphenethylamine; N-Methyl-N-(3-diethylamino-3-oxopropyl)-2C-D; N-Methyl-N-(2-diethylcarbamoylethyl)-2,5-dimethoxy-4-methylphenethylamine; N-Methyl-N-(2-diethylcarbamoylethyl)-2C-D; NM-NDEAOP-2C-D; NM-NDECE-2C-D; "Compound 4"
Identifiers
  • 3-[2-(2,5-dimethoxy-4-methylphenyl)ethyl-methylamino]-N,N-diethylpropanamide
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC19H32N2O3
Molar mass336.476 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)CCN(C)CCC1=C(C=C(C(=C1)OC)C)OC
  • InChI=1S/C19H32N2O3/c1-7-21(8-2)19(22)10-12-20(4)11-9-16-14-17(23-5)15(3)13-18(16)24-6/h13-14H,7-12H2,1-6H3
  • Key:GEVSOPBAZVTJIF-UHFFFAOYSA-N

25D-NM-NDEAOP, or 25D-NM-NDEPA, is a chemical compound of the phenethylamine and 2C families.[1][2][3] It is a simplified or partial lysergamide and is a derivative of 2C-D with a lysergic acid diethylamide (LSD)-like N-(3-diethylamino-3-oxopropyl)- substitution.[1][2][3]

Pharmacology

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Pharmacodynamics

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The compound was assessed and found to inhibit prolactin secretion in rat pituitary glands in vitro at high concentrations, suggesting that it may possess weak dopamine receptor agonist activity.[2][1] However, it was subsequently assessed in rats in vivo and, in contrast to LSD, was found to not significantly inhibit prolactin secretion.[1] Other possible activities of 25D-NM-NDEAOP, such as serotonin receptor interactions and associated effects, were not evaluated or reported.[1][2][3]

Chemistry

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The compound is a PEA-NDEPA derivative and is similar in structure to other PEA-NDEPA compounds such as DOM-NDEPA and TMA-2-NDEPA, as well as DOB-NDEPA, DOI-NDEPA, and DOTFM-NDEPA.[4] The latter three compounds have been predicted via QSAR modeling to be potent serotonin 5-HT2A receptor agonists.[4] A parent compound of 25D-NM-NEAOP is N-(3-diethylamino-3-oxopropyl)-N-methylphenethylamine (N-DEAOP-NMPEA or PEA-NM-NDEPA), which showed weak oxytocic activity in preclinical research.[5]

Chemical structures of 25D-NM-NDEAOP (25D-NM-NDEPA), DOM-NDEPA, and LSD. LSD contains the structures of 25D-NM-NDEAOP and DOM-NDEPA except their 2,5-dimethoxy- and 4-methyl- phenyl ring substitutions.

History

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25D-NDEAOP was first described in the scientific literature in 1974.[2][1]

Society and culture

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Canada

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25D-NM-NDEAOP may or may not be a controlled substance in Canada under phenethylamine blanket-ban language.[6]

See also

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References

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  1. ^ a b c d e f Rusterholz DB, Barfknecht CF, Clemens JA (January 1976). "Ergoline congeners as potential inhibitors of prolactin release. 2". Journal of Medicinal Chemistry. 19 (1): 99–102. doi:10.1021/jm00223a016. PMID 1246056.
  2. ^ a b c d e Barfknecht CF, Rusterholz DB (March 1974). "Inhibition of prolactin by ergoline congeners". Journal of Medicinal Chemistry. 17 (3): 308–312. doi:10.1021/jm00249a010. PMID 4811226.
  3. ^ a b c "3-[2-(2,5-dimethoxy-4-methylphenyl)ethyl-methylamino]-N,N-diethylpropanamide". PubChem. U.S. National Library of Medicine. Retrieved 30 March 2025.
  4. ^ a b Schulze-Alexandru M, Kovar KA, Vedani A (1999). "Quasi-atomistic Receptor Surrogates for the 5-HT2A Receptor: A 3D-QSAR Study on Hallucinogenic Substances" (PDF). Quantitative Structure-Activity Relationships. 18 (6): 548–560. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B. ISSN 0931-8771. Retrieved 1 April 2025. Table 3. New phenylalkylamine and tryptamine congeners. Cf. also Figure 5. [...] Figure 5. Molecular structures of the new 5-HT2A congeneric ligands. Cf. also Table 3. [...] Table 4. Predicted binding af®nities of new compounds, index by substance classes. [...]
  5. ^ Norris PE, Blicke FF (December 1952). "Potential ergot substitutes: esters and amides of beta-amino acids". Journal of the American Pharmaceutical Association. 41 (12): 637–639. doi:10.1002/jps.3030411204. PMID 13022416. Six esters and amides of derivatives of β-alanine which are related to lysergic acid have been prepared and tested for oxytocic activity. None of these products possess a significant oxytocic activity. [...] The purpose of this investigation was to synthesize amides and also esters of compounds (II–V) which represent fragments of the lysergic acid molecule in the hope that some of these products might possess oxytocic activity. Various modified fragments of the lysergic acid molecule have been synthesized previously; it was claimed that some of the compounds are active oxytocics (1—7). [...] Pharmacologic data indicated that none of the esters or amides of compounds II—V which were prepared possess a significant oxytocic action when compared to the clinically used oxytocics. However, the diethylamide of N-methyl-N-[β′-(3-indolyl)-ethyl]-β-alanine (IIIc) appeared to have an oxytocic activity approximately ten times stronger than that of the diethylamide of N-methyl-N-(β′-phenethyl)-β-alanine (IIc).
  6. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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